
Family-friendly vacation rentals in Chelsea
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chelsea
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

The Day-Burrill-Wadsworth-La Voix House
The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

Licensed Boston airport studio 5 stars, subway
We are a licensed & permitted Airbnb in the Boston area, ensuring a safe, reliable experience for all our guests, meeting safety & inspectional standards. Flexible early/late check in/out, please advise us of your expected check in and check out times so we can better accommodate you & your travel plans. Normal check in 3pm, normal check out 11am. Please let us know if you need parking, we provide free off street parking during your stay. Window AC in the summer. Looking forward to hosting you.

Stylish and Cozy at Revere Beach
Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔Pool ✔ Gym ✔ Patio

Studio Close to Beach, Boston, Airport & Train
Modern and cozy basement studio just 10 minutes drive from Logan Airport, 5 minutes from Revere Beach, and 14 minutes from Downtown Boston. Fully equipped with a kitchenette, full bathroom, high-speed internet, and a 75-inch Smart TV. Enjoy entertainment options like a foosball table, Xbox, and board games. Step outside to a private lounge area with a fireplace and grill. Free driveway parking and plenty of nearby restaurants make this the perfect home base for comfort, convenience, and fun.

Marblehead Tiny House
This new 360 square foot tiny house sleeps four comfortably. A mile from old town, down town, and just steps from Salem Harbor for breathtaking sunsets. The house is located in private, wooded back yard of our home. Kitchen is outfitted with small refrigerator, instant pot, air fryer, hot plate with pots and pans, microwave oven, blender, toaster, coffee maker, and electric tea kettle, as well as glasses, plates, flatware, etc for eating in. Kitchen table and chairs comfortably seats four.

10 min Logan Airport- 3Bed/ 2Bath, Sleep 7
Welcome to my charming townhouse in the heart of Chelsea. An ideal retreat for your stay near Boston. Conveniently located just a few miles away from all the Bostons attractions, my townhouse offers easy access to the best that Boston has to offer. Whether you're here for business or pleasure, you'll find everything you need for a memorable stay right at your fingertips. Book your stay at my townhouse today and experience the perfect blend of comfort and convenience for your Boston trip!

Cozy Winter Cabin Near BOS, Airport w/Parking
Private and spacious lower level 550 sq ft studio close to the city. You'll be a quick 10-20 mins drive to downtown Boston, and 30-40 mins to coastal towns, including Salem. You'll have a reserved driveway parking spot on a quiet residential street. We provide guests with a professionally cleaned cabin, plenty of towels, and coziness! We are located on a quaint and low-traffic hill, so if you are walking to the bus, it is 0.7 mi away, with inclines. Access to our home requires steps

#9 Modern Home 15 min to Boston w/ Yard & Parking
Stay in this stylish 2-story home with 3 Comfy Bedrooms + 1.5 Baths! Ideal for families or groups, it comfortably fits 6+ guests. Enjoy a fully stocked kitchen, dedicated workspace, and a private backyard with a BBQ & a fire pit. Perfectly located for exploring Boston, Cambridge, and Salem with free private parking. Your memorable stay with experienced Superhosts awaits! 📶 High-Speed Wi-Fi + Smart TVs 🚗 Private Parking for 2 Cars 🧺 In-Unit Laundry 🌆 Easy Access to Local Attractions

10 minutes to Airport-Boston-Casino (2G)
(2G)=Your place is on the 2nd floor and your color code is Green. Do Not include it to the address when you navigate to us. We have a beautiful victorian house built in 1858, owned by our family in 1911, big spaces and high ceilings are a blessing! You can stay here with your family and kids, we have a play room with some toys for fun, a living room, a bedroom and a private full bathroom with a pressure shower. Chelsea is a nice quiet place with a lot to offer.

Luxury Grand Oasis | Pool · Gym · Parking · 2BR
Discover your exclusive retreat in Everett. Immerse yourself in sleek, curated living with designer finishes and resort‑style amenities for an unforgettable stay. Highlights: • Steps from downtown Boston via easy Silver Line & Route 1 access • Sparkling pool with cabana seating and courtyard fire pits • 24/7 state‑of‑the‑art fitness center & dedicated yoga studio • Private music room, co‑working pods & on‑site community pet spa

Newly Built En Suite
Discover a stylish en-suite apartment in Woburn, MA, managed by experienced hosts. This property features a private entrance, a spacious layout with high ceilings, and a private patio. Enjoy easy access to local attractions and the convenience of a well-equipped space. Perfect for a relaxing getaway with your furry friend, this apartment offers a blend of comfort and accessibility.

Modern Suite Near Boston, Airport & Downtown
Enjoy a spacious, private suite with its own entry and free parking on Admiral's Hill. Nestled in a secure, gated community, this peaceful retreat offers stunning city views and direct access to Mary O'Malley State Park. Perfectly located minutes from Logan Airport. Easy access to downtown Boston via public transit, it’s ideal for both relaxation and convenience.
Popular amenities for Chelsea family-friendly rentals
Family-friendly home rentals with a hot tub

Nana-tucket Inn

Romantic Getaway w/private Jacuzzi• Fire Pit•

c. 1850 Farmhouse • Near Boston & Gillette

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

Beach Cottage in Scituate w/ A/C and HOT TUB

Oceanfront Pool. Close to Boston. Free Parking.

Winery Studio w/ Private Hot Tub & Wine Tasting

Headers’ Haven
Family- and pet-friendly home rentals

Sunny 3 bedroom on beach

Absolutely Gorgeous 3 Bedroom Close to Boston

Ocean Park Retreat

Flower Farm Getaway 2BR, 20 Min To Boston

Just Renovated, Private & Quiet 2 Bedroom Condo

Renovated Cozy City Getaway

Newly Renovated + Spacious Apt w/ Parking

Ocean view studio with hot tub & access to Boston
Family-friendly home rentals with a pool

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Spacious vacation unit in premium suburban town

Private Pool Retreat w/Fire Pit Near Singing Beach

Cozy Private Suite halfway between Cape & Boston

The Franklin: Wellness • Aesthetic • W/D • Gym

Country Cottage in the City

Fifa 2026-Private Pool-1 Mi to Team France HQ
When is the best time to visit Chelsea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 551 | ﺩ.ﺇ 525 | ﺩ.ﺇ 555 | ﺩ.ﺇ 687 | ﺩ.ﺇ 804 | ﺩ.ﺇ 738 | ﺩ.ﺇ 757 | ﺩ.ﺇ 753 | ﺩ.ﺇ 771 | ﺩ.ﺇ 797 | ﺩ.ﺇ 683 | ﺩ.ﺇ 628 |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
Quick stats about vacation rentals that are family-friendly in Chelsea

Total vacation rentals
Explore 100 vacation rentals in Chelsea

Nightly prices starting at
Chelsea vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

Verified guest reviews
Over 9,050 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
100 of Chelsea vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chelsea rentals

4.8 Average rating
Chelsea stays are highly rated by guests—averaging 4.8 out of 5!
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- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- Revere Beach
- Boston Seaport
- Boston University
- Gillette Stadium
- Northeastern University
- Boston Convention and Exhibition Center
- Freedom Trail
- MIT Museum
- New England Aquarium
- Canobie Lake Park
- Crane Beach
- Onset Beach
- Duxbury Beach
- Roxbury Crossing Station
- Quincy Market
- North Hampton Beach
- Museum of Fine Arts
- Prudential Center





